Shemales Porn Stories
Page 2

Leila Has a Big Secret

I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most.

It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before.

I'd stayed over at a friend's house and after a nice leisurely breakfast I headed home so that I would be back home before dark. I had to be at work the next day and wanted plenty of rest.

I was driving along Highway 1 when I first saw her. And boy, was she a vision. It had been raining all morning and the woman who stood there beside the road w... Continue»
Posted by drew1207 9 days ago  |  Categories: Fetish, Sex Humor, Shemales  |  Views: 5847  |  
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Wife Shares Shemale

"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an hour see you." She hung up.

The phone call made me really nervous.I had reasons to get nervous if not get a nervous break down. Tara and her husband owns a few restaurants in different cities across the States. I have known Tara since 6 months now since she busted me from one of the restrooms of her restaurants. Well wh... Continue»
Posted by drew1207 9 days ago  |  Categories: Anal, Fetish, Shemales  |  Views: 4272  |  
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First Date

My urges to be with a man had been growing every day, so I decided to start an online dating account, to see if any guys were interested in me. In a matter of hours, I received hundreds of messages from interested men. One in particular stood out to me. He was 6'5" and muscular and a former marine. He sent me flirty e-mails and I flirted back and sent him a few pictures. After about the 10th email he told me that he had re-read my profile and he didn't realize that I was transgender. He told me he had never been with a t-girl but that I was so sexy that he didn't even care, he needed to take m... Continue»
Posted by xjessica88x 12 days ago  |  Categories: First Time, Shemales  |  Views: 3554  |  
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The Windowcleaners

I was home alone for the weekend as my parents were out of town. I had been instructed by my online master that i had to spend the whole day as a girl (a naughty teen slut at that). No matter what i had to do that day i had to do it dressed in girly lingerie and or clothing...
I got up, showered and looked through all my outfits to decide what to wear... First of all i put on my lingerie which consisted of a white and pink spotty thong, black fishnet stockings and a black and pink teddy/basque... I had to go to the supermarket to get some groceries so i completed the look with a pair of tigh... Continue»
Posted by slut_trish 12 days ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 2274  |  
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Car Crash

I woke up feeling incredibly horny, it was still pretty early, around 5am. I really felt like doing something naughty and risky, so i decided i was going to dress up in my sexiest 'girl clothes' and go for a drive in my car. I had done this a few times before but usually only in lingerie under my ordinary male clothing.. As it was early i figured there wouldnt be many people around at that time of the morning so i thought id be a little more daring and go completly in girl mode this time...

I laid all my girly underwear and outfits out on my bed so i could decide what to wear. As it was sum... Continue»
Posted by slut_trish 12 days ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 2839  |  
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Tentacle impregnation

I had just finished a session up at the gym and began walking back to my car. It was dark out and the large car park was empty, nobody could see me. I was wearing just a tight grey leotard.

My big bulging cock showing clearly up my stomach, small wet patch from a little pre cum, my tits free, no bra, nipples erect from the cold, wobbling as I walked, along with my ass and thighs.

As I got to my car I got in and got myself comfortable, suddenly I was locked in my own car, from under my seat crawled fleshy huge tentacles in the shape of huge cocks, all dripping pre cum. They tied me to m... Continue»
Posted by drew1207 13 days ago  |  Categories: Fetish, Sex Humor, Shemales  |  Views: 3104  |  
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Charlotte and her sister go swimming

I did not write this story.

I am 18, I have a younger sibling who is 2 years younger than me called Emily. Even though she is younger than me and we both come from the same parents, she has a better body than me. She is curvy, taller than me, wider hips, small waist, amazing big round ass and huge tits. I'm a D but she is an E, almost F. She turns me on a lot, I know it's wrong but I get horny thinking of her naked.

We both love our swimming. Even though this is an awkward sport for me as I am tiny and it is hard for me to hide a big 8 inch cock. I usually tuck it between my legs pushing... Continue»
Posted by drew1207 13 days ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 5977  |  
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Charlotte and her friends little sister

I did not write this story

After a night out I stayed over at my friends sl**ping in the spare room. In the morning my friend had work and left without waking me but she told me the night before she had work and I could stay until she got home again.

Waking up in the morning I felt groggy and tired but one thing I did notice was I woke up with morning glory, I was rock solid and made a huge tent of the quilt. I needed to sort this out. I slid my hand down into my panties where it was stretching them and slid them off allowing my cock to grow to it's full size, I was so horny and instant... Continue»
Posted by drew1207 13 days ago  |  Categories: Fetish, Sex Humor, Shemales  |  Views: 4045  |  
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Walk of Shame.

As I woke, I tried to stir, to move, but in all honesty I was as thick headed as a punch d***k boxer; no thought made sense, I did not know where I was, my arms and legs were numb and I could hardly breathe....

I knew where I was. I was sure of it. I had been sent here deliberately... As I licked my dry, cracked lips which were alcohol dry and parched, there were vague memories. I had been sent here. Moaning, I tried to rise but stiff linen bed sheeting was moulded to me, it crackled as I moved making me open my eyes to accept what was around me.

The hotel room was beige, very beige and ... Continue»
Posted by CorneliaO 13 days ago  |  Categories: Shemales  |  Views: 2196  |  
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Mile High (caught in panties and pegged at 30,000

Mile High (caught in panties and pegged at thirty thousand feet)

By Mikaho, Edited by g1dnshwrgr1

I boarded the plan and was taking my seat when I noticed the most mature of the three stewardesses.  She was beautiful with a classic flair; her pencil skirt perfectly presented an hourglass waist, defined hips, and a round butt.

The image of her shapely form flitted around the edge of my thoughts as I started answering email on my phone and quickly drifted into a hyper-focused state;  oblivious to the bustle in the cabin around me until I heard her ask me to turn off my phone.  I glanced... Continue»
Posted by Shelleyisasissy 13 days ago  |  Categories: Anal, BDSM, Shemales  |  Views: 3270  |  
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Virgin no More

It was a cool, fall full-moon night and I danced in the glen beside my home, wearing my sheer white negligee and waving one of those florescent green glowsticks as I danced, giving the truckers a show.

Maybe. I doubted if they could really see anything but a white-female looking form dancing half-a-mile-away in the moonlight. Yes, I was being a cocktease.

(Isn’t a gurl supposed to flirt? Jeeeezzzzzz.)

I returned to my computer and signed off for the night, relishing in my dance as a gurl in the out-of-doors, my boobies jiggling and nipples hardening. The sheer fabric of t... Continue»
Posted by prairieFreak13 14 days ago  |  Categories: First Time, Shemales  |  Views: 1807  |  
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Halloween Pt3

My enthusiasm waivered a little once his crotch was in my face. I could see his cock straining against his sweat pants. But, I considered the alternatives: He was horny, and he was expecting relief. We were in his frat house. And he was much bigger than I was. And, I was dressed like a young woman hot for the D. If I told him no, he could easily beat the shit out of me. And then tell everyone he was fooled. God knows what his frat b*****rs would do.

Besides, he'd sucked my cock. How bad could it be? Women liked giving blow jobs, and obviously some guys did too. It's not like anyo... Continue»
Posted by TransContinental 14 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1466  |  
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My First Time with Brian.

Heya there boys and girls! My name's Nicole and i'm a pre-op transexual from the UK, by chance I came across this website about a month ago and despite noticing that most of the user's seem to be madly perverted (lol) the rest seem civil enough to the point where I thought, "why not share my stories?" Who knows? You might just get a kick out of them. ; ) x

Back when I was 17 I had been cross dressing for just over a year, I was never tall (5'5 if you must know) and didn't have a masculine frame to boot (I guess I was always meant to be a girl - clearly haha) ANYWAYS one weekend when I was o... Continue»
Posted by NicoleB90 15 days ago  |  Categories: Anal, First Time, Shemales  |  Views: 1740  |  
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fucked by indonesian ladyboys

this is a true story of what actually happened to me in bali

When i was 17 i was on holiday in bali, indonesia. i'd only had sex once prior, with a genetic girl, and i barely managed to get hard and wasn't able to cum so i knew pussy wasn't for me.
i had been clubbing several times on this trip to bali and had been hassled by numerous prostitutes while out but wasn't interested, except for one night whilst walking back to my hotel on a quiet street in legian, a deep but seductive voice called out "hello" to me from the shadows of a run down apartment block, emerging from the dark stood a ... Continue»
Posted by yuneeqboi 15 days ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 3361  |  
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Halloween Pt2

Todd, er, I mean Colette, stalked proudly out the front door, confident as hell. I hesitated, watching him, er, her, er, him, whatever, take about ten sashaying strides down the sidewalk. He'd obviously got the trick of walking in heels down, because his hips swayed ever so sexily. Hips! I suddenly realized he had hips! His waist was tapered, and he had hips. His ass looked amazing when he, she walked. (I learned later Todd had bought a waist cincher to narrow his midsection, and emphasize his hips. But I'm getting ahead of myself.)

"Damn. You look hot," that was all I could say, ... Continue»
Posted by TransContinental 20 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3033  |  
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Basketball Star & Math Tutor

The crowd cheered profusely as the Francis Marion High School Swampfoxes dominated the opposing team. The home team had been led by the five-foot-eleven-inch junior Anton Jones. The slender point guard ended the night with a triple double – 21 points, 11 steals, & 12 assists. The scouts loved him and he loved them. He was being looked at seriously by numerous Division One colleges and he had designs on the University of Kentucky. His parents were steadfast Apostolic Christians and told he would attend whatever school gave him the best scholarship. Secretly, they hope their son would make it bi... Continue»
Posted by faggyboi 21 days ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 2734  |  
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Court Date

Aubrey James Phillips sat quietly in the municipal courtroom as he waited for his destiny to be decided. He had hired a lawyer to help get him off the charges he was facing. Court was slated to begin at 2:00 p.m. so he made sure he was in place at 1:15 p.m. Twenty minutes after he arrived wearing black slacks, a light blue button down shirt, a red tie, and black Stacy Adams, in walked an extremely attractive light-skinned woman. He stared at her, but not too hard. Typically, he liked dark-skinned chicks as he was a relative red bone himself. But this lady had that indescribable characteristic ... Continue»
Posted by faggyboi 22 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2895  |  
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Cum hungry paper boy sissy

Cum hungry paper boy sissy



When I was thirteen our next door neighbor Pat offered me a summer job
helping him deliver papers and magazines. I quickly said yes and my
foster parents agreed. I liked Pat a lot as he always patted my ass when
Vance and Liz were doing something when he came over for dinner as he
smiled and winked. I loved the way it felt and smiled back as my cock got
hard.

I was light build and kept my long blonde hair in a pony tail and always
wore cut off jean shorts. I had also been jerking off and eating my
creamy delicious cum loads for over a year as I loved... Continue»
Posted by jayymie 22 days ago  |  Categories: Anal, First Time, Shemales  |  Views: 5820  |  
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Halloween Pt1

Another damn Halloween story. Pure fiction.

We were probably stoned when we came up with the idea. Todd and I had been roommates for our first two years on college, and got on well enough that we moved off campus for our junior year.

Anyway, in late September we were talking about Halloween, and trying to come up with ideas. One of us, I forget whom, suggested we go on the usual pub crawl in drag. We laughed and laughed and laughed, before laughing about some doofus who fell into a swimming pool on some blooper show on TV. And then we laughed some more.

A couple of days la... Continue»
Posted by TransContinental 22 days ago  |  Categories: Shemales  |  Views: 1766  |  
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Fantasy of a Fantasy

It wasn't that I was opposed to man-on-man sex. It's that I wasn't for it. I mean, it didn't get me hard, but it didn't turn me off either. I know this not because I sought it out, but a gal I dated for a while confessed she loved gay porn, and had a fantasy of a threesome, where she'd back off and watch the two guys go at it. This was years ago, of course, and being the open minded guy I was, I said I'd consider it, if, big if, the other dude was okay.

But, as I said, this was years ago, and we never got around to trying. She went her way, I went mine, and eventually found myself in a... Continue»
Posted by TransContinental 22 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2165  |  
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